6 mins

It seems there are two types of remote workers, but it’s changed in the last few years.

Remote working in the early days were for those who had something: either an endorsement or network. The best remote jobs were available to people who had already ‘proved’ their worth, typically from stints working at a big name company and often with a successful exit. For those remote workers, they get to set the terms and rely on heavily opportunistic hiring. They have their quality of life set up, the house overlooking the beach, the experience of successful exits meant the hiring company was eager to make exceptions. Those exceptions typically sound like, ‘We need someone who can scale this distributed system to deal with our reliability problems!’ and someone says, ‘I know the perfect guy [they’re nearly all male] but he’s remote out of [insert any paradise]’. The leaders scratch their chins, then figure that for someone with this much maturity, experience, and potential value they can make an exception. Now that company is ‘remote friendly’, with the key word being ‘friendly’. You need to be friends with someone there to make it work.

Looking beyond past experience

Sometimes the right resume and network is enough to signal to a company it’s a safe-enough remote hire. I worked with enough great people and I didn’t even properly interview for nearly ten years. This model won’t diversify teams, doesn’t help companies build the remote-first muscle, and it certainly doesn’t capture the value of what remote work is supposed to solve for: expanding into talent pools we wouldn’t otherwise have access to. And by talent pools, I mean people that don’t fit the mold of the San Francisco-startup hustler.

The reason why San Francisco, and other talent-dense markets, are an easy and safe place to hire from is because the candidates have shifted the burden of discovery to themselves. Every company wants to find people with drive, grit, and motivation. What better way to filter for that then only looking at people who are already living where that’s part of the culture? There are a lot of people in the world for whom moving is just not a viable option. There are also people just as talented and bright, but the culture and environment of somewhere like San Francisco isn’t something that works for them, as humans.

I was in the heart of the .com bubble, but it burst for me when I realized that every time I went out to dinner or for coffee I heard about some startup and how they were crushing it, it was actually crushing me. Living close to my family, where my kids are raised next door to their grandparents, where nearly all my local friends don’t even know what I do, is important to me and my mental health. Because without that buffer, I don’t do my best work; I burn myself out. But I have the credentials, I have the experience, and I have the network. When I interview, people can identify my experience. I feel, and look, familiar and comfortable; I’m a safe hire.

People are different, our conversations will be, too

The greatest value of remote work is to work with people different than yourself. However, when we’re faced with people unlike us, it can be difficult to know how to assess their talents and skills, which can cause issues. And we certainly don’t know how to address the mysteries of culture fit, drive, or whether they’re going to hustle the way we expect them to.

Being remote, there really is a risk for mishires. You can’t see when people are struggling and stuck, which means you need practices in place that help you effectively lead remote teams. It’s hard, it takes work, and the more opportunistic, well-endorsed remote hires you’ve made before that started with the ‘I know the perfect guy’ made it less important to build those practices.

So, now the company supports remote work, but somehow the only people you are really successfully recruiting, interviewing, and hiring seem a little too similar to the ones you’ve already hired. Inclusive practices are a prerequisite to figuring out effective remote hiring, but it’s only the first step. The next step is outreach and understanding. If you’re only hiring experienced, tenured remote folks, there is more work to do. Before hiring, ensure that less experienced and less represented people are well supported and are just as likely to succeed as someone in the office would be. Once that’s in place, it’s safe to hire more people.

When we can hire in places where we don’t have offices, we’re going to meet people that are different from us. Their experience and talents will look different. It took me a while to really figure out how to get better at talking to a wide variety of people from various backgrounds. I’m fortunate that the recruiting team I work with now is, by far, the best. Not only are they good at talking to strangers, they’re also good at helping others learn to do it well. I think most recruiters are skilled at this, and it took me too long to get them to teach me.

Building rapport and fostering openness

The first step is recognizing there is a gap that needs bridging. We have to break ourselves out of our expectations that great candidates look like the previous pool of great candidates. This means paying attention to different signals, different behaviors, different patterns, and also reflecting on how we approach the conversations and show up. Before we can meaningfully understand a stranger’s drive, ambition, and experience, we need to build enough rapport to get that level of conversation.

We’re here for work, and not to make friends, but underpinning both is a relationship that must be built by mutual understanding. The best way to build this understanding is to find where the worlds come together, which still happens with someone who has never visited San Francisco: asking people to describe the work they’re most excited about, and being genuinely curious to hear them talk more about it. When building rapport with someone, getting them to talk more is key; focus on collaborating in the excitement they have in their work.

I’ve never met someone who hadn’t worked on something they were excited about, but I have met plenty of people who think that what they’re excited about isn’t interesting to me without a lot of prodding. I’m never disappointed when I finally get someone to talk about what was challenging and the opportunities they found, even if they started with a dismissive disclaimer of, ‘Well, the scale is so small, it’s no big deal…’ As someone that strives to build great teams, it is my job to get people to open up and share their excitement.

Once I hear a potential candidate’s story of the work they’re proud of, we tend to have enough rapport that I can start to think about recruiting. Prematurely moving a conversation into a recruiting stage is just another way we prematurely optimize. We still have to ease in, because someone who was reluctant to share what they’re most excited about likely has a narrative about you, too. Taking some time to understand their perspective pays dividends. If they expect to be looked down upon, that can change how questions are perceived. Even if you intend something as a genuine question, it may not land that way. Take the time to get it right, and then you’ll get a relationship that you can build on.

The best recruiting starts with relationships – and relationships are harder to build when we start from further away. The companies and teams that get good at building relationships will be best at recruiting; it’s a competitive advantage and you get to meet awesome people. There are no downsides – you either find a great candidate or learn a bit more about someone and what’s exciting in the world. It’s work, but it’s worth it. Good luck on your journey to meeting great people and having a more inclusive remote hiring experience!